NP-MRD: Showing NP-Card for 6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one (NP0226502)

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Record Information

Version

2.0

Created at

2022-09-06 05:33:32 UTC

Updated at

2022-09-06 05:33:32 UTC

NP-MRD ID

NP0226502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one

Description

6-Acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-2H,3H,4H,5H,10H-pyrano[2,3-g]phthalazin-5-one belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 6-Acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-2H,3H,4H,5H,10H-pyrano[2,3-g]phthalazin-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231522522D          

 34 37  0  0  0  0            999 V2000
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M  END

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M  END
> <DATABASE_ID>
NP0226502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=NN=CC2=C1C(=O)C1=C(OC(C)(C)C(Cl)C1)C2(O)CC1C(C)(O)CCC(Cl)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32Cl2N2O5/c1-12(30)19-18-14(11-28-29-19)25(33,10-15-22(2,3)16(26)7-8-24(15,6)32)21-13(20(18)31)9-17(27)23(4,5)34-21/h11,15-17,32-33H,7-10H2,1-6H3

> <INCHI_KEY>
FKSQFICQDFLQEW-UHFFFAOYSA-N

> <FORMULA>
C25H32Cl2N2O5

> <MOLECULAR_WEIGHT>
511.44

> <EXACT_MASS>
510.1688275

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.38059656437649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-2H,3H,4H,5H,10H-pyrano[2,3-g]phthalazin-5-one

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
1.8228325140000008

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.76565251800633

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20235507150729

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4735818768384297

> <JCHEM_POLAR_SURFACE_AREA>
109.61000000000001

> <JCHEM_REFRACTIVITY>
131.9917

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3H,4H-pyrano[2,3-g]phthalazin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.278  -2.130   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.724  -2.130   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.908  -3.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.631  -4.795   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.844  -3.847   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.775  -5.826   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.815  -6.101   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0       4.538  -7.461   0.000  0.00  0.00          Cl+0
HETATM   30  C   UNK     0       2.276  -6.048   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.553  -4.688   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.369  -3.382   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.092  -2.521   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.369  -1.842   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21   13    8   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂Cl₂N₂O₅

Average Mass

511.4400 Da

Monoisotopic Mass

510.16883 Da

IUPAC Name

6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-2H,3H,4H,5H,10H-pyrano[2,3-g]phthalazin-5-one

Traditional Name

6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3H,4H-pyrano[2,3-g]phthalazin-5-one

CAS Registry Number

Not Available

SMILES

CC(=O)C1=NN=CC2=C1C(=O)C1=C(OC(C)(C)C(Cl)C1)C2(O)CC1C(C)(O)CCC(Cl)C1(C)C

InChI Identifier

InChI=1S/C25H32Cl2N2O5/c1-12(30)19-18-14(11-28-29-19)25(33,10-15-22(2,3)16(26)7-8-24(15,6)32)21-13(20(18)31)9-17(27)23(4,5)34-21/h11,15-17,32-33H,7-10H2,1-6H3

InChI Key

FKSQFICQDFLQEW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Cyclohexanol
Cyclohexyl halide
Pyridazine
Cyclic alcohol
Tertiary alcohol
Vinylogous ester
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Oxacycle
Alkyl halide
Organic nitrogen compound
Alkyl chloride
Organic oxide
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.34	ALOGPS
logP	1.82	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.99 m³·mol⁻¹	ChemAxon
Polarizability	51.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73061242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one (NP0226502)

MOL for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

3D MOL for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

3D SDF for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

3D-SDF for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

PDB for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

3D PDB for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

SMILES for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

INCHI for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

Structure for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)

3D Structure for NP0226502 (6-acetyl-3-chloro-10-[(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl)methyl]-10-hydroxy-2,2-dimethyl-3h,4h-pyrano[2,3-g]phthalazin-5-one)